|Intimacy Level||Ex-Boyfriend and Ex-Girlfriend (Implied Sexual)|
|Started Dating||Before Father Figure (1) (301)|
|Dating Status||Broken Up in Holiday (2) (312)|
In Father Figure (1), at Christine Nelson's baby shower. Caitlin Ryan accidentally sat on a plate of cake and Sydney offered to help clean it up and then introduced herself. Caitlin also did in return and revealed that she was an old friend of Christine's. This brought up the fact that she also knew Joey. Caitlin explained that Joey and herself had an on and off relationship during high school, and then suggested that this may continue due to the fact that she had now moved back to Toronto for the year. Sydney was silent and then Joey came along and kissed her. Caitlin was slightly embarrassed after what she had said about her and Joey getting back together and started to walk away.
In U Got the Look, Sydney and Joey were hanging out in his kitchen, drinking wine together, under the dimmed lights until they heard extremely loud music playing. She asked Joey what the noise was and he told her that it was his stepson Craig Manning and his new band playing in the garage. Joey and Sydney walked out to the garage to watch them play. Joey got into it and wanted to help them find their sound. He brought out his keyboard and started "jamming" with them, much to their discomfort. Sydney, Ashley Kerwin and Angela Jeremiah watched him reliving his teenage years and were all embarrassed.
In Pride (2), Snake discovered that he had leukemia and feeling bad for him, Sydney and Joey dropped off dinner at his house while he was at his doctor's appointment with Spike. Joey and Sydney told Snake and his family that they just stopped by to make him a nice home-cooked meal and then started making their way out. Snake told them to stay for dinner, but Joey, Sydney and Spike reminded him that he had just had a long day and that he should eat by himself and rest. Trying to stay active and positive, Snake insisted that they stay to eat.
In Against All Odds, Joey and Sydney were at home with Craig. They were all quietly sitting on the couch together watching a film and Joey asked Craig what he was doing at home on a Friday night. Craig then walked out to meet Manny Santos at a rave, leaving Sydney and Joey happy to finally get some alone time together.In Holiday (1), Joey's relationship with Sydney begins to evolve more. Joey, Craig and Sydney are first seen at the house, putting up the Christmas tree. That night, they have a Christmas party with the Simpson-Nelson family, Caitlin and Ashley. Caitlin was happy for Joey and Sydney, but she knew that she still had feelings for him deep down. The next day, Sydney helps Angela get ready for her Christmas pageant ice show. She surprises her with a new dress she made for her pageant. Sydney apologizes to Angela for the fact that she can't make it to the show because she has to work commitment. In return, she promises to take Angela Boxing Day shopping to make up for her missing it. When Joey and Sydney return home and Sydney sees Angie's costume dirty, Caitlin tells Sydney not to be mad at Angie but Sydney says that she's not mad at Angie and glares at Caitlin.
In Holiday (2), after Caitlin kisses Joey, she goes to Spike for advise on what to do. Spike tells Caitlin to write her feelings on a letter and give it to Joey. When Caitlin puts her letter in Joey's slot, she then tries to go back for it but can't reach it. She tries to get inside the house through the window but gets stuck. Joey and Sydney return home and find Caitlin stuck in the window. After helping her get out, Sydney then talks to Caitlin alone. She tells Caitlin that she knows that she still has feelings for Joey but then tells her that Joey and his family only need her, not Caitlin. She then calls Caitlin a klutz blast from the past. However, Craig overhead Sydney talking to Caitlin and found Caitlin's letter. Caitlin then grabs her letter from Craig and runs out. She then starts ripping her letter and starts crying. Craig later tells Joey of what Sydney said to Caitlin and Joey confronts her. Joey asks Sydney why would she try to make Caitlin go away. Sydney explains and then asks Joey if he loves her more than Caitlin. Joey doesn't answer and looks down. Sydney gets the message and then leaves.
In Time Stands Still (1), Joey, in his home, being told by his realtor that his open house is the day after tomorrow and that he has to clean. He is obviously desperate to sell his house, asking his realtor, Helen, what else he can do besides clean to ensure the sale. After work, Joey comes home to find his ex-girlfriend, Sydney at his house as a result of Craig calling her. Craig has told her about their money problems and Sydney wants to help Joey sell his home. Sydney ends up leaving since Joey seems practically speechless and somewhat upset about her being there suddenly. The next day, Craig is just as sick but decides to go to school after Joey yells at him for calling Sydney. Joey obviously feels embarrassed about his financial situation. Craig tells Joey that he called Sydney because she would at least sell the house for good money. Sydney comes back to Joey's house. Obviously, Joey decided the Craig was right about taking Sydney's help. Joey apologizes about how things ended with them. Sydney brushes his apology off and suggests he make an atmosphere for the open house using music and maybe baking a pie in the oven. Her expertise in real estate is already evident.
In Time Stands Still (2), Sydney sold Joey's house to Caitlin and the house is saved. This is Sydney's final appearance.
- Start Up: Sometime before Father Figure (1) (301)
- Broke Up: Holiday (2) (312)
- Reason: Sydney was rude to Caitlin, for whom Joey still had feelings.